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href="https://ca.wikipedia.org/wiki/Mauve%C3%AFna" title="Mauveïna – Catalan" lang="ca" hreflang="ca" data-title="Mauveïna" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target"><span>Català</span></a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Mauveine" title="Mauveine – German" lang="de" hreflang="de" data-title="Mauveine" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target"><span>Deutsch</span></a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/Aniliinlilla" title="Aniliinlilla – Estonian" lang="et" hreflang="et" data-title="Aniliinlilla" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target"><span>Eesti</span></a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Mauve%C3%ADna" title="Mauveína – Spanish" lang="es" hreflang="es" data-title="Mauveína" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target"><span>Español</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Mauv%C3%A9ine" title="Mauvéine – French" lang="fr" hreflang="fr" data-title="Mauvéine" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%AA%A8%EB%B2%A0%EC%9D%B8" title="모베인 – Korean" lang="ko" hreflang="ko" data-title="모베인" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target"><span>한국어</span></a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Mauvein" title="Mauvein – Croatian" lang="hr" hreflang="hr" data-title="Mauvein" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target"><span>Hrvatski</span></a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Porpora_di_anilina" title="Porpora di anilina – Italian" lang="it" hreflang="it" data-title="Porpora di anilina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target"><span>Italiano</span></a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Mauve%C3%AFne" title="Mauveïne – Dutch" lang="nl" hreflang="nl" data-title="Mauveïne" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target"><span>Nederlands</span></a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%83%A2%E3%83%BC%E3%83%96" title="モーブ – Japanese" lang="ja" hreflang="ja" data-title="モーブ" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target"><span>日本語</span></a></li><li class="interlanguage-link interwiki-or mw-list-item"><a href="https://or.wikipedia.org/wiki/%E0%AC%95%E0%AD%83%E0%AC%A4%E0%AD%8D%E0%AC%B0%E0%AC%BF%E0%AC%AE_%E0%AC%B0%E0%AC%9E%E0%AD%8D%E0%AC%9C%E0%AC%95" title="କୃତ୍ରିମ ରଞ୍ଜକ – Odia" lang="or" hreflang="or" data-title="କୃତ୍ରିମ ରଞ୍ଜକ" data-language-autonym="ଓଡ଼ିଆ" data-language-local-name="Odia" class="interlanguage-link-target"><span>ଓଡ଼ିଆ</span></a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Mauve%C3%ADna" title="Mauveína – Portuguese" lang="pt" hreflang="pt" data-title="Mauveína" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%9C%D0%BE%D0%B2%D0%B5%D0%B8%D0%BD" title="Мовеин – Russian" lang="ru" hreflang="ru" data-title="Мовеин" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target"><span>Русский</span></a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Mauveine" title="Mauveine – Simple English" lang="en-simple" hreflang="en-simple" data-title="Mauveine" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target"><span>Simple English</span></a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Anilinsko_barvilo" title="Anilinsko barvilo – Slovenian" lang="sl" hreflang="sl" data-title="Anilinsko barvilo" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target"><span>Slovenščina</span></a></li><li class="interlanguage-link interwiki-fi mw-list-item"><a href="https://fi.wikipedia.org/wiki/Mauveiini" title="Mauveiini – Finnish" lang="fi" hreflang="fi" data-title="Mauveiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target"><span>Suomi</span></a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Mauvein" title="Mauvein – Swedish" lang="sv" hreflang="sv" data-title="Mauvein" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target"><span>Svenska</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%9C%D0%BE%D0%B2%D0%B5%D1%97%D0%BD" title="Мовеїн – Ukrainian" lang="uk" hreflang="uk" data-title="Мовеїн" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a 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class="vector-body" aria-labelledby="firstHeading" data-mw-ve-target-container> <div class="vector-body-before-content"> <div class="mw-indicators"> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Synthetic dye</div> <figure class="mw-default-size mw-halign-right" typeof="mw:File/Thumb"><a href="/wiki/File:Mauv2.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Mauv2.jpg/220px-Mauv2.jpg" decoding="async" width="220" height="291" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/df/Mauv2.jpg/330px-Mauv2.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/d/df/Mauv2.jpg 2x" data-file-width="372" data-file-height="492" /></a><figcaption>Letter from Perkin's son, with a sample of dyed silk</figcaption></figure> <p><b>Mauveine</b>, also known as <b>aniline purple</b> and <b>Perkin's mauve</b>, was one of the first synthetic <a href="/wiki/Dye" title="Dye">dyes</a>.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It was discovered <a href="/wiki/Serendipity" title="Serendipity">serendipitously</a> by <a href="/wiki/William_Henry_Perkin" title="William Henry Perkin">William Henry Perkin</a> in 1856 while he was attempting to synthesise the phytochemical <a href="/wiki/Quinine" title="Quinine">quinine</a> for the treatment of <a href="/wiki/Malaria" title="Malaria">malaria</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> It is also among the first chemical dyes to have been mass-produced.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mauveine&action=edit&section=1" title="Edit section: Chemistry"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Mauveine is a mixture of four related <a href="/wiki/Aromaticity" title="Aromaticity">aromatic</a> compounds differing in number and placement of <a href="/wiki/Methyl_group" title="Methyl group">methyl groups</a>. Its <a href="/wiki/Organic_synthesis" title="Organic synthesis">organic synthesis</a> involves dissolving <a href="/wiki/Aniline" title="Aniline">aniline</a>, <a href="/wiki/P-toluidine" class="mw-redirect" title="P-toluidine"><i>p</i>-toluidine</a>, and <a href="/wiki/O-toluidine" class="mw-redirect" title="O-toluidine"><i>o</i>-toluidine</a> in <a href="/wiki/Sulfuric_acid" title="Sulfuric acid">sulfuric acid</a> and water in a roughly 1:1:2 ratio, then adding <a href="/wiki/Potassium_dichromate" title="Potassium dichromate">potassium dichromate</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p><i>Mauveine A</i> (<style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">C<sub class="template-chem2-sub">26</sub>H<sub class="template-chem2-sub">23</sub>N<span class="template-chem2-su"><span>+</span><span>4</span></span>X<sup class="template-chem2-sup">−</sup></span>) incorporates 2 molecules of <a href="/wiki/Aniline" title="Aniline">aniline</a>, one of <i>p</i>-toluidine, and one of <i>o</i>-toluidine. <i>Mauveine B</i> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410" /><span class="chemf nowrap">C<sub class="template-chem2-sub">27</sub>H<sub class="template-chem2-sub">25</sub>N<span class="template-chem2-su"><span>+</span><span>4</span></span>X<sup class="template-chem2-sup">−</sup></span>) incorporates one molecule each of aniline, <i>p</i>-toluidine, and two of <i>o</i>-toluidine. In 1879, Perkin showed mauveine B related to <a href="/wiki/Safranine" class="mw-redirect" title="Safranine">safranines</a> by <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidative</a>/<a href="/wiki/Redox" title="Redox">reductive</a> loss of the <i>p</i>-tolyl group.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> In fact, <a href="/wiki/Safranine" class="mw-redirect" title="Safranine">safranine</a> is a 2,8-dimethyl <a href="/wiki/Phenazine" title="Phenazine">phenazinium</a> salt, whereas the <a href="/w/index.php?title=Parasafranine&action=edit&redlink=1" class="new" title="Parasafranine (page does not exist)">parasafranine</a> produced by Perkin is presumed<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> to be the 1,8- (or 2,9-) dimethyl <a href="/wiki/Isomer" title="Isomer">isomer</a>. </p><p>The molecular structure of mauveine proved difficult to determine, finally being identified in 1994.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In 2007, two more were isolated and identified: <i>mauveine B2</i>, an isomer of mauveine B with methyl on different aryl group, and <i>mauveine C</i>, which has one more <i>p</i>-methyl group than mauveine A.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> </p> <ul class="gallery mw-gallery-traditional"> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Mauveine_a_skeletal_org.svg" class="mw-file-description" title="Skeletal formula of mauveine A"><img alt="Skeletal formula of mauveine A" src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Mauveine_a_skeletal_org.svg/120px-Mauveine_a_skeletal_org.svg.png" decoding="async" width="120" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Mauveine_a_skeletal_org.svg/180px-Mauveine_a_skeletal_org.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Mauveine_a_skeletal_org.svg/240px-Mauveine_a_skeletal_org.svg.png 2x" data-file-width="512" data-file-height="366" /></a></span></div> <div class="gallerytext"><a href="/wiki/Skeletal_formula" title="Skeletal formula">Skeletal formula</a> of mauveine A</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Mauveine_b_skeletal_org.svg" class="mw-file-description" title="Skeletal formula of mauveine B"><img alt="Skeletal formula of mauveine B" src="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Mauveine_b_skeletal_org.svg/120px-Mauveine_b_skeletal_org.svg.png" decoding="async" width="120" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/16/Mauveine_b_skeletal_org.svg/180px-Mauveine_b_skeletal_org.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/16/Mauveine_b_skeletal_org.svg/240px-Mauveine_b_skeletal_org.svg.png 2x" data-file-width="512" data-file-height="405" /></a></span></div> <div class="gallerytext">Skeletal formula of mauveine B</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Mauveine_b2_skeletal_org.svg" class="mw-file-description" title="Skeletal formula of mauveine B2"><img alt="Skeletal formula of mauveine B2" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Mauveine_b2_skeletal_org.svg/120px-Mauveine_b2_skeletal_org.svg.png" decoding="async" width="120" height="86" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/55/Mauveine_b2_skeletal_org.svg/180px-Mauveine_b2_skeletal_org.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/55/Mauveine_b2_skeletal_org.svg/240px-Mauveine_b2_skeletal_org.svg.png 2x" data-file-width="512" data-file-height="366" /></a></span></div> <div class="gallerytext">Skeletal formula of mauveine B2</div> </li> <li class="gallerybox" style="width: 155px"> <div class="thumb" style="width: 150px; height: 150px;"><span typeof="mw:File"><a href="/wiki/File:Mauveine_c_skeletal_org.svg" class="mw-file-description" title="Skeletal formula of mauveine C"><img alt="Skeletal formula of mauveine C" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Mauveine_c_skeletal_org.svg/120px-Mauveine_c_skeletal_org.svg.png" decoding="async" width="120" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Mauveine_c_skeletal_org.svg/180px-Mauveine_c_skeletal_org.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5a/Mauveine_c_skeletal_org.svg/240px-Mauveine_c_skeletal_org.svg.png 2x" data-file-width="512" data-file-height="405" /></a></span></div> <div class="gallerytext">Skeletal formula of mauveine C</div> </li> </ul> <p>In 2008, additional mauveines and pseudomauveines were discovered, bringing the total number of these compounds up to 12.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> In 2015 a crystal structure was reported for the first time.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mauveine&action=edit&section=2" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Charles_Rees_(in_mauveine-dyed_bowtie).jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Charles_Rees_%28in_mauveine-dyed_bowtie%29.jpg/220px-Charles_Rees_%28in_mauveine-dyed_bowtie%29.jpg" decoding="async" width="220" height="291" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/00/Charles_Rees_%28in_mauveine-dyed_bowtie%29.jpg/330px-Charles_Rees_%28in_mauveine-dyed_bowtie%29.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/0/00/Charles_Rees_%28in_mauveine-dyed_bowtie%29.jpg 2x" data-file-width="373" data-file-height="493" /></a><figcaption>Professor <a href="/wiki/Charles_Rees" title="Charles Rees">Charles Rees</a>—wearing a bow tie dyed with an original sample of mauveine—holding an <a href="/wiki/Royal_Society_of_Chemistry" title="Royal Society of Chemistry">RSC</a> journal named after Perkin</figcaption></figure> <div class="color_swatch" style="background: white; border: solid 1px black; float: right; margin: 0 .5em 1em 1.5em; font-size: 90%; text-align: center; width: 12em;"> <div class="mw-no-invert" style="background: #8D029B; border-bottom: solid 1px black; color: #000000; height: 9em" title="#8D029B"></div> <p>Mauveine <code>#8D029B</code><br />#8D029B </p> </div> <p>In 1856, <a href="/wiki/Sir_William_Henry_Perkin" class="mw-redirect" title="Sir William Henry Perkin">William Henry Perkin</a>, then age 18, was given a challenge by his professor, <a href="/wiki/August_Wilhelm_von_Hofmann" title="August Wilhelm von Hofmann">August Wilhelm von Hofmann</a>, to synthesize <a href="/wiki/Quinine" title="Quinine">quinine</a>. In one attempt, Perkin <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidized</a> aniline using <a href="/wiki/Potassium_dichromate" title="Potassium dichromate">potassium dichromate</a>, whose <a href="/wiki/Toluidine" title="Toluidine">toluidine</a> impurities reacted with the aniline and yielded a black solid, suggesting a "failed" organic synthesis. Cleaning the flask with alcohol, Perkin noticed <a href="/wiki/Purple" title="Purple">purple</a> portions of the solution. </p><p>Suitable as a dye of <a href="/wiki/Silk" title="Silk">silk</a> and other <a href="/wiki/Textile" title="Textile">textiles</a>, it was <a href="/wiki/Patent" title="Patent">patented</a> by Perkin, who the next year opened a dyeworks mass-producing it at <a href="/wiki/Greenford" title="Greenford">Greenford</a> on the banks of the <a href="/wiki/Grand_Union_Canal" title="Grand Union Canal">Grand Union Canal</a> in <a href="/wiki/Middlesex" title="Middlesex">Middlesex</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It was originally called <i>aniline purple</i>. In 1859, it was named <i><a href="/wiki/Mauve" title="Mauve">mauve</a></i> in England via the French name for the <a href="/wiki/Malva" title="Malva">mallow</a> flower, and chemists later called it mauveine.<sup id="cite_ref-matthew2004_14-0" class="reference"><a href="#cite_note-matthew2004-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Between 1859 and 1861, mauve became a fashion must have. The weekly journal <i><a href="/wiki/All_the_Year_Round" title="All the Year Round">All the Year Round</a></i> described women wearing the colour as "all flying countryward, like so many migrating birds of purple paradise".<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Punch_(magazine)" title="Punch (magazine)"><i>Punch</i> magazine</a> published cartoons poking fun at the huge popularity of the colour “The Mauve Measles are spreading to so serious an extent that it is high time to consider by what means [they] may be checked.”<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> </p><p>By 1870, demand succumbed to newer synthetic colors in the <a href="/wiki/Synthetic_dye" class="mw-redirect" title="Synthetic dye">synthetic dye</a> industry launched by mauveine. </p><p>In the early 20th century, the U.S. National Association of Confectioners permitted mauveine as a food coloring with a variety of equivalent names: <i>rosolan</i>, <i>violet paste</i>, <i>chrome violet</i>, <i>anilin violet</i>, <i>anilin purple</i>, <i>Perkin's violet</i>, <i>indisin</i>, <i>phenamin</i>, <i>purpurin</i> and <i>lydin</i>.<sup id="cite_ref-Leffman_19-0" class="reference"><a href="#cite_note-Leffman-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p><p>Laborers in the aniline dye industry were later found to be at increased risk of bladder cancer, specifically <a href="/wiki/Transitional_cell_carcinoma" title="Transitional cell carcinoma">transitional cell carcinoma</a>, yet by the 1950s, the synthetic dye industry had <a href="/wiki/Aniline#History" title="Aniline">helped transform medicine</a>, including cancer treatment.<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mauveine&action=edit&section=3" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist reflist-columns references-column-width" style="column-width: 30em;"> <ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFHubner2006" class="citation journal cs1">Hubner (2006). "History – 150 Years of mauveine". <i>Chemie in unserer Zeit</i>. <b>40</b> (4): <span class="nowrap">274–</span>275. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fciuz.200690054">10.1002/ciuz.200690054</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Chemie+in+unserer+Zeit&rft.atitle=History+%E2%80%93+150+Years+of+mauveine&rft.volume=40&rft.issue=4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E274-%3C%2Fspan%3E275&rft.date=2006&rft_id=info%3Adoi%2F10.1002%2Fciuz.200690054&rft.au=Hubner&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMauveine" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFAnthony_S._Travis1990" class="citation journal cs1">Anthony S. Travis (1990). 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London: John Murray. p. 21. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/9781473630819" title="Special:BookSources/9781473630819"><bdi>9781473630819</bdi></a>. <a href="/wiki/OCLC_(identifier)" class="mw-redirect" title="OCLC (identifier)">OCLC</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/oclc/936144129">936144129</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=The+Secret+Lives+of+Colour&rft.place=London&rft.pages=21&rft.pub=John+Murray&rft.date=2016&rft_id=info%3Aoclcnum%2F936144129&rft.isbn=9781473630819&rft.aulast=St.+Clair&rft.aufirst=Kassia&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMauveine" class="Z3988"></span></span> </li> <li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHicks2017" class="citation web cs1">Hicks, Jan (2017-08-25). <a rel="nofollow" class="external text" href="https://blog.scienceandindustrymuseum.org.uk/worlds-first-synthetic-dye/">"William Henry Perkin and the world's first synthetic dye"</a>. <i>Science and Industry Museum blog</i><span class="reference-accessdate">. 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(2015). <a rel="nofollow" class="external text" href="https://doi.org/10.3184%2F174751915X14474318419130">"Syntheses and Structures of Pseudo-Mauveine Picrate and 3-Phenylamino-5-(2-Methylphenyl)-7-Amino-8-Methylphenazinium Picrate Ethanol Mono-Solvate: The First Crystal Structures of a Mauveine Chromophore and a Synthetic Derivative"</a>. <i>Journal of Chemical Research</i>. <b>39</b> (12): <span class="nowrap">711–</span>718. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.3184%2F174751915X14474318419130">10.3184/174751915X14474318419130</a></span>. <a href="/wiki/Hdl_(identifier)" class="mw-redirect" title="Hdl (identifier)">hdl</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://hdl.handle.net/2164%2F5423">2164/5423</a></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Chemical+Research&rft.atitle=Syntheses+and+Structures+of+Pseudo-Mauveine+Picrate+and+3-Phenylamino-5-%282-Methylphenyl%29-7-Amino-8-Methylphenazinium+Picrate+Ethanol+Mono-Solvate%3A+The+First+Crystal+Structures+of+a+Mauveine+Chromophore+and+a+Synthetic+Derivative&rft.volume=39&rft.issue=12&rft.pages=%3Cspan+class%3D%22nowrap%22%3E711-%3C%2Fspan%3E718&rft.date=2015&rft_id=info%3Ahdl%2F2164%2F5423&rft_id=info%3Adoi%2F10.3184%2F174751915X14474318419130&rft.aulast=Plater&rft.aufirst=M.+John&rft.au=Harrison%2C+William+T.+A.&rft.au=Rzepa%2C+Henry+S.&rft_id=https%3A%2F%2Fdoi.org%2F10.3184%252F174751915X14474318419130&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMauveine" class="Z3988"></span></span> </li> <li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text">Google Earth location: <a rel="nofollow" class="external text" href="http://www.ch.ic.ac.uk/motm/perkin/mauveine.kml">Download</a></span> </li> <li id="cite_note-matthew2004-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-matthew2004_14-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMatthewHoward_Harrison2004" class="citation book cs1">Matthew, H.C.G.; Howard Harrison, Brian (2004). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/isbn_0198613857"><i>Oxford Dictionary of National Biography: In Association with the British Academy</i></a></span>. <a href="/wiki/Oxford_University_Press" title="Oxford University Press">Oxford University Press</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-19-861393-8" title="Special:BookSources/0-19-861393-8"><bdi>0-19-861393-8</bdi></a>. <q>perkins tyrian.purple.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Oxford+Dictionary+of+National+Biography%3A+In+Association+with+the+British+Academy&rft.pub=Oxford+University+Press&rft.date=2004&rft.isbn=0-19-861393-8&rft.aulast=Matthew&rft.aufirst=H.C.G.&rft.au=Howard+Harrison%2C+Brian&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fisbn_0198613857&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMauveine" class="Z3988"></span></span> </li> <li id="cite_note-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-15">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFGarfield2000" class="citation news cs1">Garfield, Simon (2000-09-21). <a rel="nofollow" class="external text" href="https://www.theguardian.com/books/2000/sep/21/fiction.simongarfield">"Simon Garfield on mauve"</a>. <i>The Guardian</i>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0261-3077">0261-3077</a><span class="reference-accessdate">. Retrieved <span class="nowrap">2020-05-27</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Guardian&rft.atitle=Simon+Garfield+on+mauve&rft.date=2000-09-21&rft.issn=0261-3077&rft.aulast=Garfield&rft.aufirst=Simon&rft_id=https%3A%2F%2Fwww.theguardian.com%2Fbooks%2F2000%2Fsep%2F21%2Ffiction.simongarfield&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMauveine" class="Z3988"></span></span> </li> <li id="cite_note-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-16">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBlakemore" class="citation web cs1">Blakemore, Erin. <a rel="nofollow" class="external text" href="https://www.smithsonianmag.com/smart-news/how-malaria-gave-us-mauve-180958427/">"How Malaria Gave Us Mauve"</a>. <i>Smithsonian Magazine</i><span class="reference-accessdate">. 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Blakiston's Son & Co. p. <a rel="nofollow" class="external text" href="https://archive.org/details/selectmethodsin01beamgoog/page/n80">77</a>. <q>perkins tyrian.purple.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Select+Methods+in+Food+Analysis&rft.place=Philadelphia&rft.pages=77&rft.pub=P.+Blakiston%27s+Son+%26+Co.&rft.date=1901&rft.aulast=Leffmann&rft.aufirst=Henry&rft.au=William+Beam&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fselectmethodsin01beamgoog&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMauveine" class="Z3988"></span></span> </li> <li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFCartwright1983" class="citation journal cs1">Cartwright, R.A. (1983). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1569142">"Historical and modern epidemiological studies on populations exposed to N-substituted aryl compounds"</a>. <i>Environmental Health Perspectives</i>. <b>49</b>: <span class="nowrap">13–</span>19. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1289%2Fehp.834913">10.1289/ehp.834913</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1569142">1569142</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6339220">6339220</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Environmental+Health+Perspectives&rft.atitle=Historical+and+modern+epidemiological+studies+on+populations+exposed+to+N-substituted+aryl+compounds&rft.volume=49&rft.pages=%3Cspan+class%3D%22nowrap%22%3E13-%3C%2Fspan%3E19&rft.date=1983&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1569142%23id-name%3DPMC&rft_id=info%3Apmid%2F6339220&rft_id=info%3Adoi%2F10.1289%2Fehp.834913&rft.aulast=Cartwright&rft.aufirst=R.A.&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC1569142&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMauveine" class="Z3988"></span></span> </li> <li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text">John E Lesch, <i>The First Miracle Drugs: How the Sulfa Drugs Transformed Medicine</i> (New York: Oxford University Press, 2007), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=dFgZRlRy5ScC&pg=PA202">pp 202–3</a></span> </li> <li id="cite_note-22"><span class="mw-cite-backlink"><b><a href="#cite_ref-22">^</a></b></span> <span class="reference-text">D J Th Wagener, <i>The History of Oncology</i> (Houten: Springer, 2009), <a rel="nofollow" class="external text" href="https://books.google.com/books?id=53fmwacXu44C&pg=PA150">pp 150–1</a>.</span> </li> </ol></div> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mauveine&action=edit&section=4" title="Edit section: Further reading"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFSimon_Garfield2002" class="citation book cs1">Simon Garfield (2002). <span class="id-lock-registration" title="Free registration required"><a rel="nofollow" class="external text" href="https://archive.org/details/mauvehowonemanin00garf"><i>Mauve: How One Man Invented a Color That Changed the World</i></a></span>. W. W. Norton & Company. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0393323139" title="Special:BookSources/978-0393323139"><bdi>978-0393323139</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Mauve%3A+How+One+Man+Invented+a+Color+That+Changed+the+World&rft.pub=W.+W.+Norton+%26+Company&rft.date=2002&rft.isbn=978-0393323139&rft.au=Simon+Garfield&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Fmauvehowonemanin00garf&rfr_id=info%3Asid%2Fen.wikipedia.org%3AMauveine" class="Z3988"></span></li></ul> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Mauveine&action=edit&section=5" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><a rel="nofollow" class="external text" href="http://www.rsc.org/Chemsoc/Activities/Perkin/index.asp">Perkin anniversary website</a><sup> <a rel="nofollow" class="external text" href="https://web.archive.org/web/20061111102500/http://www.rsc.org/Chemsoc/Activities/Perkin/index.asp">Archived</a> 2006-11-11 at the <a href="/wiki/Wayback_Machine" title="Wayback Machine">Wayback Machine</a></sup></li> <li>Rotatable 3D models of mauveine are <a rel="nofollow" class="external text" href="http://www.ch.ic.ac.uk/motm/perkin.html">available</a> using <a href="/wiki/Jmol" title="Jmol">Jmol</a></li></ul>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Mauveine&oldid=1223684271">https://en.wikipedia.org/w/index.php?title=Mauveine&oldid=1223684271</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Azin_dyes" title="Category:Azin dyes">Azin dyes</a></li><li><a href="/wiki/Category:English_inventions" title="Category:English inventions">English inventions</a></li><li><a href="/wiki/Category:History_of_chemistry" title="Category:History of chemistry">History of chemistry</a></li><li><a href="/wiki/Category:Organic_chemistry" title="Category:Organic chemistry">Organic chemistry</a></li><li><a href="/wiki/Category:Shades_of_violet" title="Category:Shades of violet">Shades of violet</a></li><li><a href="/wiki/Category:Phenazines" title="Category:Phenazines">Phenazines</a></li><li><a href="/wiki/Category:Quaternary_ammonium_compounds" title="Category:Quaternary ammonium compounds">Quaternary ammonium compounds</a></li><li><a href="/wiki/Category:Chemical_mixtures" title="Category:Chemical mixtures">Chemical mixtures</a></li><li><a href="/wiki/Category:1856_introductions" title="Category:1856 introductions">1856 introductions</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:Webarchive_template_wayback_links" title="Category:Webarchive template wayback links">Webarchive template wayback links</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 13 May 2024, at 18:00<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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